PT86023B - Processo para a preparacao de composicoes que aumentam o fluxo transdermico, contendo uma 1-alquilazaciclo-heptan-2-ona ou uma cis-olefina - Google Patents

Processo para a preparacao de composicoes que aumentam o fluxo transdermico, contendo uma 1-alquilazaciclo-heptan-2-ona ou uma cis-olefina Download PDF

Info

Publication number: PT86023B
Authority: PT; Portugal
Prior art keywords: ethanol; cis; acid; piroxicam; alkyl
Prior art date: 1986-10-31

Application number

PT86023A

Other languages

English (en)

Portuguese (pt)

Other versions

PT86023A (en

Inventor

Michael Lee Francoeur

Russell Owen Potts

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-10-31

Filing date

1987-10-29

Publication date

1990-07-31

1987-10-29 Application filed by Pfizer filed Critical Pfizer

1987-11-01 Publication of PT86023A publication Critical patent/PT86023A/pt

1990-07-31 Publication of PT86023B publication Critical patent/PT86023B/pt

Links

239000000203 mixture Substances 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 160
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000000651 prodrug Substances 0.000 claims abstract description 27
229940002612 prodrug Drugs 0.000 claims abstract description 27
239000003961 penetration enhancing agent Substances 0.000 claims abstract description 16
241000282414 Homo sapiens Species 0.000 claims abstract description 14
241001465754 Metazoa Species 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims abstract description 12
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 42
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 41
229960002702 piroxicam Drugs 0.000 claims description 41
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 40
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 40
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 40
239000005642 Oleic acid Substances 0.000 claims description 40
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 40
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 27
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 20
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 claims description 18
229960001381 glipizide Drugs 0.000 claims description 18
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 16
229960004889 salicylic acid Drugs 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
229960001389 doxazosin Drugs 0.000 claims description 12
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
-1 allodipine Chemical compound 0.000 claims description 11
229960000528 amlodipine Drugs 0.000 claims description 11
229960001047 methyl salicylate Drugs 0.000 claims description 10
230000035515 penetration Effects 0.000 claims description 10
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 9
229960001680 ibuprofen Drugs 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 7
UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002091 cationic group Chemical group 0.000 claims description 5
UWHZIFQPPBDJPM-FPLPWBNLSA-N cis-vaccenic acid Chemical compound CCCCCC\C=C/CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-FPLPWBNLSA-N 0.000 claims description 5
230000001965 increasing effect Effects 0.000 claims description 4
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract description 2
230000002708 enhancing effect Effects 0.000 abstract description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
230000004907 flux Effects 0.000 abstract 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
239000000872 buffer Substances 0.000 description 40
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 38
235000021313 oleic acid Nutrition 0.000 description 37
210000003491 skin Anatomy 0.000 description 33
239000003981 vehicle Substances 0.000 description 30
OHHDIOKRWWOXMT-UHFFFAOYSA-N trazodone hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 OHHDIOKRWWOXMT-UHFFFAOYSA-N 0.000 description 25
238000011282 treatment Methods 0.000 description 23
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ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 10
235000014113 dietary fatty acids Nutrition 0.000 description 10
238000002474 experimental method Methods 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
229930195729 fatty acid Natural products 0.000 description 10
150000004665 fatty acids Chemical class 0.000 description 10
206010020772 Hypertension Diseases 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000000338 in vitro Methods 0.000 description 9
238000009472 formulation Methods 0.000 description 8
206010012601 diabetes mellitus Diseases 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000009792 diffusion process Methods 0.000 description 6
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239000003814 drug Substances 0.000 description 6
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238000004458 analytical method Methods 0.000 description 5
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239000012047 saturated solution Substances 0.000 description 5
206010002383 Angina Pectoris Diseases 0.000 description 4
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
208000025747 Rheumatic disease Diseases 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
230000004044 response Effects 0.000 description 4
230000000552 rheumatic effect Effects 0.000 description 4
230000007704 transition Effects 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 3
102000004142 Trypsin Human genes 0.000 description 3
108090000631 Trypsin Proteins 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000011088 calibration curve Methods 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001514 detection method Methods 0.000 description 3
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
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201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
VJECBOKJABCYMF-UHFFFAOYSA-N doxazosin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 VJECBOKJABCYMF-UHFFFAOYSA-N 0.000 description 3
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238000002329 infrared spectrum Methods 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
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239000011780 sodium chloride Substances 0.000 description 3
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
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239000012588 trypsin Substances 0.000 description 3
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125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
125000005313 fatty acid group Chemical group 0.000 description 1
229960002390 flurbiprofen Drugs 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000008311 hydrophilic ointment Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
YWWVWXASSLXJHU-WAYWQWQTSA-N myristoleic acid Chemical compound CCCC\C=C/CCCCCCCC(O)=O YWWVWXASSLXJHU-WAYWQWQTSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000036407 pain Effects 0.000 description 1
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
231100000435 percutaneous penetration Toxicity 0.000 description 1
CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 1
UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000003643 water by type Substances 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Dermatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Materials For Medical Uses (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

PT86023A 1986-10-31 1987-10-29 Processo para a preparacao de composicoes que aumentam o fluxo transdermico, contendo uma 1-alquilazaciclo-heptan-2-ona ou uma cis-olefina PT86023B (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US92564186A	1986-10-31	1986-10-31

Publications (2)

Publication Number	Publication Date
PT86023A PT86023A (en)	1987-11-01
PT86023B true PT86023B (pt)	1990-07-31

Family

ID=25452022

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT86023A PT86023B (pt)	1986-10-31	1987-10-29	Processo para a preparacao de composicoes que aumentam o fluxo transdermico, contendo uma 1-alquilazaciclo-heptan-2-ona ou uma cis-olefina

Country Status (24)

Country	Link
EP (1)	EP0271983B1 (de)
JP (1)	JPH0757725B2 (de)
KR (1)	KR900003697B1 (de)
CN (1)	CN87107548A (de)
AT (1)	ATE64306T1 (de)
AU (1)	AU595948B2 (de)
CA (1)	CA1338008C (de)
DE (1)	DE3770786D1 (de)
DK (1)	DK568187A (de)
EG (1)	EG18324A (de)
ES (1)	ES2031518T3 (de)
GR (1)	GR3002137T3 (de)
HU (1)	HU197993B (de)
IE (1)	IE60379B1 (de)
IL (1)	IL84269A (de)
MX (1)	MX171058B (de)
MY (1)	MY102980A (de)
NO (1)	NO175617C (de)
NZ (1)	NZ222346A (de)
PH (1)	PH25498A (de)
PT (1)	PT86023B (de)
RU (2)	RU1836078C (de)
YU (1)	YU46755B (de)
ZA (1)	ZA878161B (de)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5196416A (en) *	1987-08-28	1993-03-23	Eli Lilly And Company	Transdermal flux-enhancing pharmaceutical compositions comprising azone, ethanol and water
ZA886218B (en) *	1987-08-28	1990-04-25	Lilly Co Eli	Permeation enhancement compositions
ATE80313T1 (de) *	1988-02-29	1992-09-15	Pfizer	Mittel zur erhoehung des transdermalen penetrationsflusses.
CH679119A5 (de) *	1988-05-13	1991-12-31	Sandoz Ag
US5024843A (en) *	1989-09-05	1991-06-18	Alza Corporation	Oral hypoglycemic glipizide granulation
US5023085A (en) *	1989-11-29	1991-06-11	Pfizer Inc.	Transdermal flux enhancers in combination with iontophoresis in topical administration of pharmaceuticals
US5149719A (en) *	1990-04-27	1992-09-22	Minnesota Mining And Manufacturing Company	Composition for transdermal penetration of medicaments
WO1992017185A1 (en) *	1991-03-29	1992-10-15	University Of Florida	Targeted drug delivery via mixed phosphate derivatives
ES2160623T3 (es) *	1992-12-31	2001-11-16	Sunkyong Ind Ltd	Composiciones farmaceuticas mejoradas para la penetracion en la piel de piroxicam.
DE4341572C1 (de) *	1993-12-07	1995-06-22	Univ Dresden Tech	Zahnriemengetriebe
TW304167B (de) *	1995-01-30	1997-05-01	Lilly Co Eli
GB2306885B (en) *	1995-11-08	1999-07-14	Reckitt & Colmann Prod Ltd	Supersaturated Pharmaceutical Compositions
EP0849265A1 (de) *	1996-12-20	1998-06-24	HEUMANN PHARMA GmbH	Neue polymorphe Form von Doxazosin-Mesylat (Form II)
JP2000143540A (ja) *	1998-11-06	2000-05-23	Bristol Myers Squibb Co	非ステロイド系消炎鎮痛薬含有外用剤
US7198801B2 (en)	2000-08-03	2007-04-03	Antares Pharma Ipl Ag	Formulations for transdermal or transmucosal application
ATE485837T1 (de)	2000-08-03	2010-11-15	Antares Pharma Ipl Ag	Zusammensetzung zur transdermalen und/oder transmukosalen verabreichung von wirkstoffen, die ausreichende therapeutische spiegel garantiert
US8980290B2 (en)	2000-08-03	2015-03-17	Antares Pharma Ipl Ag	Transdermal compositions for anticholinergic agents
US6503894B1 (en)	2000-08-30	2003-01-07	Unimed Pharmaceuticals, Inc.	Pharmaceutical composition and method for treating hypogonadism
RU2229286C2 (ru) *	2002-05-27	2004-05-27	Пятигорская государственная фармацевтическая академия	Мазь ибупрофена, приготовленная на полиэтиленоксидной основе, обладающая противовоспалительным действием
RU2261086C2 (ru) *	2003-05-26	2005-09-27	Горский государственный аграрный университет (ГГАУ)	Лечебная мазь для животных
JP4626202B2 (ja) *	2003-07-16	2011-02-02	大正製薬株式会社	ピロキシカム含有外用消炎鎮痛剤組成物
ATE534373T1 (de)	2003-10-10	2011-12-15	Antares Pharma Ipl Ag	Transdermale pharmazeutische formulierung zur minimierung von rückständen auf der haut
US7425340B2 (en)	2004-05-07	2008-09-16	Antares Pharma Ipl Ag	Permeation enhancing compositions for anticholinergic agents
US8067399B2 (en)	2005-05-27	2011-11-29	Antares Pharma Ipl Ag	Method and apparatus for transdermal or transmucosal application of testosterone
CN102225046A (zh) *	2005-08-05	2011-10-26	努沃研究公司	透皮释药剂型
GEP20125432B (en)	2005-10-12	2012-03-26	Unimed Pharmaceuticals Llc	Improved testosterone gel and use thereof
FR2892410B1 (fr) *	2005-10-21	2010-10-15	Fabre Pierre Dermo Cosmetique	Nouveaux hydro-acides gras insatures et leur utilisation dermo cosmetologique
CN101426475A (zh)	2006-04-21	2009-05-06	安塔雷斯制药Ipl股份公司	使用用于经皮或经粘膜应用的制剂治疗热潮红的方法
CN102256604A (zh) *	2008-12-17	2011-11-23	株式会社医药处方	稳定的氨氯地平含水口服制剂
US20130123221A1 (en) *	2011-05-16	2013-05-16	Dale L. Pearlman	Compositions and methods for the treatment of skin diseases
US8580286B2 (en)	2012-03-16	2013-11-12	Dale L. Pearlman	Compositions and methods for the treatment of skin diseases
JP7515582B2 (ja)	2019-11-06	2024-07-12	スマーテックトピカル，インコーポレイテッド	シクロオキシゲナーゼ阻害剤の局所配合剤およびその使用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1538903A (en) *	1975-04-11	1979-01-24	Nelson Res & Dev	Carrier for a topically applied physiologically active agent or cosmetic agent
US4316893A (en) *	1975-06-19	1982-02-23	Nelson Research & Development Co.	Vehicle composition containing 1-substituted azacycloalkan-2-ones
US4405616A (en) *	1975-06-19	1983-09-20	Nelson Research & Development Company	Penetration enhancers for transdermal drug delivery of systemic agents
BE843140A (fr) *	1975-06-19	1976-10-18		Aazacycloalcan-2-ones 1-substituees et compositions pharmaceutiques contenant ces composes a titre d'excipients
EP0127426A1 (de) *	1983-05-23	1984-12-05	Takeda Chemical Industries, Ltd.	Perkutane pharmazeutische Zusammensetzungen zur äusserlichen Anwendung
DK243084A (da) *	1983-05-26	1984-11-27	Takeda Chemical Industries Ltd	Perkutane farmaceutiske praeparater til udvortes brug
US4537776A (en) *	1983-06-21	1985-08-27	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing N-(2-hydroxyethyl) pyrrolidone
US4557934A (en) *	1983-06-21	1985-12-10	The Procter & Gamble Company	Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one

1987
- 1987-10-17 MY MYPI87002939A patent/MY102980A/en unknown
- 1987-10-25 IL IL84269A patent/IL84269A/xx not_active IP Right Cessation
- 1987-10-27 AT AT87309459T patent/ATE64306T1/de not_active IP Right Cessation
- 1987-10-27 ES ES198787309459T patent/ES2031518T3/es not_active Expired - Lifetime
- 1987-10-27 DE DE8787309459T patent/DE3770786D1/de not_active Expired - Lifetime
- 1987-10-27 EP EP87309459A patent/EP0271983B1/de not_active Expired - Lifetime
- 1987-10-28 YU YU196487A patent/YU46755B/sh unknown
- 1987-10-28 IE IE289687A patent/IE60379B1/en not_active IP Right Cessation
- 1987-10-29 PH PH36001A patent/PH25498A/en unknown
- 1987-10-29 PT PT86023A patent/PT86023B/pt not_active IP Right Cessation
- 1987-10-29 CA CA000550540A patent/CA1338008C/en not_active Expired - Fee Related
- 1987-10-29 EG EG618/87A patent/EG18324A/xx active
- 1987-10-29 CN CN198787107548A patent/CN87107548A/zh active Pending
- 1987-10-29 NZ NZ222346A patent/NZ222346A/xx unknown
- 1987-10-30 RU SU874203579A patent/RU1836078C/ru active
- 1987-10-30 HU HU874898A patent/HU197993B/hu not_active IP Right Cessation
- 1987-10-30 DK DK568187A patent/DK568187A/da not_active Application Discontinuation
- 1987-10-30 AU AU80542/87A patent/AU595948B2/en not_active Ceased
- 1987-10-30 JP JP62275581A patent/JPH0757725B2/ja not_active Expired - Lifetime
- 1987-10-30 ZA ZA878161A patent/ZA878161B/xx unknown
- 1987-10-30 MX MX026963A patent/MX171058B/es unknown
- 1987-10-30 NO NO874531A patent/NO175617C/no unknown
- 1987-10-30 KR KR1019870012096A patent/KR900003697B1/ko not_active Expired
1991
- 1991-06-13 GR GR91400807T patent/GR3002137T3/el unknown
- 1991-12-23 RU SU5010466A patent/RU2107515C1/ru active

Also Published As

Publication number	Publication date
IL84269A (en)	1991-08-16
PT86023A (en)	1987-11-01
YU196487A (sh)	1993-05-28
EG18324A (en)	1992-09-30
ES2031518T3 (es)	1992-12-16
NO874531L (no)	1988-05-02
ATE64306T1 (de)	1991-06-15
CA1338008C (en)	1996-01-30
EP0271983B1 (de)	1991-06-12
ZA878161B (en)	1989-06-28
NO874531D0 (no)	1987-10-30
NZ222346A (en)	1990-08-28
RU1836078C (ru)	1993-08-23
DK568187A (da)	1988-05-01
KR880004823A (ko)	1988-06-27
YU46755B (sh)	1994-05-10
JPH0757725B2 (ja)	1995-06-21
HUT45403A (en)	1988-07-28
AU595948B2 (en)	1990-04-12
IE872896L (en)	1988-04-30
IL84269A0 (en)	1988-03-31
IE60379B1 (en)	1994-07-13
JPS63122631A (ja)	1988-05-26
GR3002137T3 (en)	1992-12-30
DE3770786D1 (de)	1991-07-18
HU197993B (en)	1989-07-28
MY102980A (en)	1993-03-31
NO175617B (de)	1994-08-01
RU2107515C1 (ru)	1998-03-27
PH25498A (en)	1991-07-24
CN87107548A (zh)	1988-05-11
AU8054287A (en)	1988-05-05
KR900003697B1 (ko)	1990-05-30
NO175617C (no)	1994-11-09
MX171058B (es)	1993-09-27
EP0271983A1 (de)	1988-06-22
DK568187D0 (da)	1987-10-30

Legal Events

Date

Code

Title

Description

1999-11-30

MM3A

Annulment or lapse

Free format text: LAPSE DUE TO NON-PAYMENT OF FEES

Effective date: 19990731

Publication	Publication Date	Title
PT86023B (pt)	1990-07-31	Processo para a preparacao de composicoes que aumentam o fluxo transdermico, contendo uma 1-alquilazaciclo-heptan-2-ona ou uma cis-olefina
US5391548A (en)	1995-02-21	Transdermal flux enhancing compositions to treat hypertension, diabetes and angina pectoris
ES2673219T3 (es)	2018-06-20	Composición para la entrega transdérmica de agentes activos
CA2373821C (en)	2003-10-07	Topical compositions for prostaglandin e1 delivery
US3969516A (en)	1976-07-13	Composition and method for treatment of acne
AU627580B2 (en)	1992-08-27	Pharmaceutical vehicles for reducing transdermal flux
US6239177B1 (en)	2001-05-29	Tranilast-containing preparation for external application and method of producing the same
PT1510213E (pt)	2009-02-12	Sistemas de melhoramento de penetração e reduzida irritação incluíndo testosterona
NZ208597A (en)	1987-02-20	A penetration-enhancing topical pharmaceutical composition comprising 1-dodecylazacycloheptan-2-one
HU207441B (en)	1993-04-28	Method for producing therapeutical preparation applicable for systematic feeding through the skin containing deprenyl as active ingredient
JPS60224638A (ja)	1985-11-09	経皮吸収促進剤およびこれを含有する外用剤
US20070275943A1 (en)	2007-11-29	Method and Composition for Treatment or Prophylaxis of Amyloidosis Disorders
FI92650C (fi)	1994-12-27	Menetelmä ihon kautta tapahtuvaa virtausta lisäävän farmaseuttisen valmisteen valmistamiseksi
JPH08175986A (ja)	1996-07-09	経皮活性を示す５−アミノレブリン酸含有薬学組成物
JPH03500287A (ja)	1991-01-24	１‐オキソ‐またはチオヒドロカルビル置換アザシクロアルカンからなる組成物
RU2165265C2 (ru)	2001-04-20	Усилители абсорбции для фармацевтических композиций местного применения
CZ102797A3 (cs)	1998-10-14	Sloučeniny na bázi omega-aminokyselin, způsob jejich přípravy jejich použití jako akcelerantů transdermální penetrace a akceleranty transdermální penetrace těmito sloučeninami tvořené
JPH0764754B2 (ja)	1995-07-12	経皮吸収促進剤及びこれを含有する皮膚外用剤
US5314906A (en)	1994-05-24	Derivatives of physostigmine, their use and pharmaceutical formulations containing them
US5900412A (en)	1999-05-04	Percutaneous/transdermal delivery of ASA and antithrombotic therapies based thereon
JPH0478620B2 (de)	1992-12-11
JPH02152921A (ja)	1990-06-12	経皮吸収外用製剤
WO2005079855A1 (es)	2005-09-01	Composicion promotora de penetracion a base de esteres de acidos grasos de sacarosa